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Montecalvo started her legal career as a trial attorney in the United States Department of Justice Tax Division from 2000 to 2004. From 2004 to 2020, she served as an assistant public defender in the Rhode Island Public Defender's Office; she served in multiple roles within the office including as a trial attorney from 2004 to 2010, as an appellate attorney from 2010 to 2014 and as chief of the appellate division from 2014 to 2020. In March 2020, Montecalvo was nominated by Rhode Island GovernorGina Raimondo to serve as the Public Defender of Rhode Island.
Federal judicial service
On April 27, 2022, President Joe Biden announced his intent to nominate Montecalvo to serve as a United States circuit judge for the First Circuit. Her nomination was praised by Senators Jack Reed and Sheldon Whitehouse. On May 19, 2022, her nomination was sent to the Senate. President Biden nominated Montecalvo to the seat to be vacated by Judge O. Rogeriee Thompson, who announced her intent to assume senior status upon confirmation of a successor. On May 25, 2022, a hearing on her nomination was held before the Senate Judiciary Committee. On June 16, 2022, her nomination was reported out of committee by a 12–10 vote. On September 13, 2022, the United States Senate invoked cloture on her nomination by a 51–45 vote. On September 14, 2022, her nomination was confirmed by a 52–47 vote. Montecalvo was the sixth public defender nominated by President Biden to be confirmed as a U.S. circuit judge, handing Biden the record for placing the most nominees with that kind of experience onto the circuit courts. She received her judicial commission on September 20, 2022.
Personal life
Montecalvo lives in Barrington, Rhode Island, with her husband, Craig V. Montecalvo, and their son.